Formic Acid → HCID 89553803, compound

HRID 590385Notes

Reaction equation

HRID 590385 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]#N)=[CH:13][C:8]=2[NH:7][C:6]1=[O:16].C(O)=[O:18]>O>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:18])=[CH:13][C:8]=2[NH:7][C:6]1=[O:16]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 89553841HCID 89553841, compound2×

Product 1

HCID 89553803HCID 89553803, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 930 mg (4.28 mmol) of 1-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile (Intermediate 13) and 949 mg of Ni—Al alloy 1:1 in 7.3 ml of 75% formic acid in water is stirred at 90° C. for 6.5 hr. After filtration, the residue is again dissolved in 7.3 ml of 75% formic acid, 949 mg of Ni—Al alloy are added and the system is stirred at 90° C. for 1 hr. After filtration, 5 ml of 2N NaOH and 5 ml of EtOH are added and the system is stirred at rt overnight. The pH is made 6-7 by addition of 2N HCl and the solution is concentrated. The residue is chromatographically purified over silicagel eluting with hexane/EtOH (100/0 to 0/100). 0.91 g of pure title compound are obtained (96% yield).

Workup

  1. filtrationAfter filtration
  2. dissolutionthe residue is again dissolved in 7.3 ml of 75% formic acid
  3. addition949 mg of Ni—Al alloy are added
  4. stirringthe system is stirred at 90° C. for 1 hr
  5. filtrationAfter filtration, 5 ml of 2N NaOH and 5 ml of EtOH
  6. additionare added
  7. stirringthe system is stirred at rt overnight
  8. additionby addition of 2N HCl
  9. concentrationthe solution is concentrated
  10. customThe residue is chromatographically purified over silicagel
  11. washeluting with hexane/EtOH (100/0 to 0/100)

Sources & evidence

ORD record
ord-2036852fe22043f19b06014fd99c04db
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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